Recognizing the inherent value in outdoor play and learning for young children, we focused upon the practices and perspectives of adults at an early childhood center as the outdoor play areas were transformed into outdoor classrooms. A salient finding emerging from the data exhibited a gap between constructivist child-led theories of play and learning and the changing needs for greater adult-led learning in the altered outdoor environment. Disparate attitudes towards greater adult intervention in children's play existed between parents, teachers, and administrators, as children and staff transitioned and acclimated to the new outdoor classroom. Using ethnographically grounded data collection, researchers interpret these findings to suggest that while teachers maintain a strong preference for child-led learning, the changing outdoor space requires increased adult-led activities and intentional environmental education goals and training.